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Top 10 Toughest Interview Questions… and how to answer them!



Job Interview

Job interviews can be tough…

Damn tough.

Anyone can answer the easy interview questions… but what about the HARD ones?

“What is your greatest weakness?”

“What don’t you want me to know about you?”

“What is the one question you were hoping I wouldn’t ask?”


How the heck do you answer these questions?

I’m about to show you…

In this article we’re going to look at the top 10 most difficult interview questions and:

  • Why the interviewer asks the question
  • What the interviewer really wants to know
  • What NOT to say
  • How to answer the question

What follows are some of the most difficult questions you could possibly get asked in an interview. These are the toughest of the tough. The worst of the worst.

If you can handle these questions the rest of the interview will be easy…

10. Why have you found difficulty getting a job?

Job Interview

Another variation of this question: “Why have you been out of work for so long?”

What the interviewer really wants to know

“If you’re so good: Why does no one else want to hire you?”

“Is there something wrong with you I should know about?”

It’s a fair question and there can be a lot of valid reasons for it.

I strongly recommend that you save yourself a lot of hassle before the interview by filling in the gaps on your CV explaining what you’ve been doing during the break so the interviewer doesn’t assume the worst and think that you’ve been sitting at home for months doing nothing.

If you took time off to study – add it to your CV.

If you did some volunteer work – add it to your CV.

If you spent time travelling overseas – add it to your CV.

If you started your own business – add it to your CV.

If you took time off to start a family – add it to your CV.

You want to make your time off sound busy and worthwhile, as if you achieved a lot and kept busy, not like you’ve been sitting at home doing nothing.

If you’ve been looking for a job unsuccessfully for months you can talk about market conditions OR you can position it the other way and speak about the fact that you’ve been holding out for the RIGHT job and not just ‘any’ job. (If you do this you need to explain in detail why the job you are interviewing for is the right job for you). Also, if you’ve turned down job offers you should explain why.

PS: Another related question you should also be ready to answer is:

“Why were you laid off/made redundant/terminated?”

There are many valid reasons why this might have happened. Maybe the company you worked for downsized, restructured or went out of business. Maybe the project you were working on was shelved. Maybe you were one of hundreds of people who were laid off or made redundant due to outsourcing. Whatever it is, be ready to clarify the situation.

9. Why should I hire you and not someone else?

Job Interview

You might have all of the required qualifications, skills and experience, but what if the other applicants do too?

I see this all the time in recruitment. Lots of candidates are great. Lots of candidates tick every box. But as they say in “The Highlander”: There can be ONLY ONE!

What the interviewer really wants to know

“What makes you the BEST person for the job?”

“Why are you the MOST qualified candidate?”

“What can you bring to the table that no one else can?”

In reality you don’t know who you’re up against or who else has applied for the job so all you can do is talk about your strengths and achievements and why you would be an asset to the company.


  • Know the job description and key selection criteria in depth and what’s most important to the employer
  • Address each point detailing how you meet each of the criteria and talk about your achievements and strengths citing specific examples: “I was the number one recruiter at Goldman Sachs for a reason. I work hard, I’m a quick learner, I take direction well, I’m fast and adaptable, my bosses and colleagues love me, I put the company first, and I have an extremely strong track record of results.”

If you can clearly demonstrate to the interviewer an understanding of the industry, their company, their competitors, and the challenges, problems and opportunities associated with the job you are applying for, you will make it easy for them to hire you and you will definitely standout from your competitors.

8. What do you like least about your job?

Job Interview

Another variation of this question is:

“What would you change about your current/previous job?”

No matter how much you like your job there is always something (if not lots of things) you would probably like to change or improve. Maybe it’s the hours. Maybe it’s the flexibility. Maybe it’s the responsibilities. Maybe it’s your colleagues or your boss!

Why interviewers ask this question

  • To see how you honestly feel about your job. Do you like what you do? Are you really passionate about it? Or is there a certain aspect of your job that you really dislike that is going to be a significant part of the job you are applying for?

I remember interviewing one of my former colleagues for a job in recruitment and asking him this question and he said he liked “everything” about recruitment.

I tried to make it safe for him to tell me the truth by telling him what I liked least: “The thing I like least about working in recruitment is that the process often moves far too slowly. Once I present a CV to a client it often takes them days – if not weeks to review it and provide feedback which I can then pass on to the candidate. Even though I’m good at managing expectations with my candidates I feel like half of my job is just chasing up clients for feedback trying to make them move quicker.”

That’s a truthful answer.


  • Don’t lie and pretend you love EVERYTHING about your job (like my former colleague did)
  • Don’t bitch and moan about all of the things you didn’t like about your previous job (Listing multiple things will only make you seem negative)
  • You also have to be careful when answering this question not to mention something that will be a significant part of the job you are interviewing for (Don’t say “demanding customers”  or “long hours” if that’s just a part of the job/industry you are working in)

Answers to avoid:

  • My boss
  • My colleagues
  • The hours

Even if these are the real answers!


  • A good answer should focus on something your current/previous job doesn’t have, that this new job does have. (Ideally this will be the real reason you applied for the job in the first place, because it will give you something such as growth or advancement that your current job doesn’t)
  • Talk about something you truly dislike that is highly unlikely to be a part of the job you are applying for (lack of challenge or room for growth if you are stepping up into a highly challenging role)
  • Speak about the fact that your previous job didn’t allow you to play to your strengths but this new job does. For example: You could talk about excessive meetings or paperwork keeping you away from clients if you’re in sales.

Ideally, when you talk about what you didn’t like, you will also say what you did about it. Maybe what you liked least about your previous job was inefficient training for newbies so you decided to step up into a leadership role to assist with the induction and on-boarding process for new starters.

Employers want someone who is part of the solution not part of the problem. Anyone can complain but how many people actually do something to solve the problem?

7. Surprise Question

Job Interview

No matter how well prepared you are for an interview, there is almost always one random question that will catch you off guard and throw you off your game.

This question will be different from candidate to candidate depending on your CV and experience.

My best advice to predict this question (and for interview preparation in general) is to put yourself in the shoes of the interviewer and look at your CV from their perspective.

What questions would you ask you to trip you up?

What might you be concerned about on your CV?

What would you like to know?

Think of the top 5 toughest questions you would ask you and have an answer up your sleeve ready just in case.

6. Tell me about a time you had conflict with a co-worker? (and how you resolved it)

Conflict is an unavoidable fact of life. Personalities clash. Everyone has their own perspective. Everyone thinks they’re right and everyone wants to be right.

Sometimes we even have conflict with friends at work. We share the same vision, but we have different ideas and disagree as to how to go about it.

Why interviewers ask questions about conflict:

  • To understand how you deal with conflict in the workplace. Do you avoid it? Are you the cause of it? Do you provoke it? Are you too passive? Or too aggressive?
  • Can you deal with conflict in a calm and professional manner without losing your cool and creating drama in the workplace? (Not many people can)
  • Can you take ownership and responsibility for your part in a conflict or will you point the finger and blame others like 99% of other people? Are you part of the problem or part of the solution?


  • Don’t give an example in which you obviously contributed to the conflict
  • Don’t point fingers or put all of the blame on the other person
  • Don’t get down into the nitty gritty as to who was right/who was wrong/who was to blame
  • Don’t make personal attacks or attack the character of the other person (The interviewer isn’t asking this question because they’re interested in what character flaws your ex-workmates have)
  • Don’t speak with emotion or negativity
  • Don’t give an example in which you tried to ignore or avoid addressing the conflict
  • Don’t give an example of a conflict which was left unresolved
  • Don’t give an example in which you escalated the problem to a manager, since the interviewer has asked what YOU did to resolve the conflict – not your manager


  • Give an example of a professional conflict that was fixed, not ignored or left unresolved
  • Give an example that demonstrates assertiveness and proactivity, not anger and aggression or avoidance towards the conflict
  • Focus on what you did to resolve the conflict

For example: “I had a disagreement with a colleague about the best way to pitch to an important client, so I suggested we go out for coffee to discuss the pros and cons of each approach, and in the end we both agreed to compromise and we came up with a solution that included both of our ideas.”

You want to demonstrate in your answer that you can remain professional even if a colleague (or manager) gets personal. You are not the cause of conflict, but at the same time, you will not react badly if it happens.

For any behavioral type interview question – which we’ll cover in depth next week, you’ll want to use the S.T.A.R method:

S.T.A.R – Situation, Task, Action, Result

Situation – What was the situation?

Task – What tasks were involved?

Action – What did you do? What actions did you take to achieve the result?

Result – What was the result?

5. Tell me about a time you had to work with a difficult co-worker

Job Interview

Another variation of this question:

“Tell me about a time you worked with someone you didn’t like.”  

It would be nice if we lived in a world where everyone got along with everyone else, but that’s not real life.

Sometimes you just don’t like someone. Sometimes people just don’t like you.

Everyone has worked with someone difficult, or someone they didn’t like. Maybe it was a boss. Maybe it was a colleague. Working with people you don’t like is a fact of life. I’ve worked with a few and I know you have too. Some people are annoying. Others are dumb, lazy or rude.

Why interviewers ask questions about difficult co-workers:

  • To see if you can work alongside someone difficult or someone you don’t like
  • To see if you are a team player who will put the company first or if you are likely to let your own personal feelings about someone get in the way of the goals of the company
  • To find out what kind of person you consider as ‘difficult’. Was it a workplace bully? Was it someone disrespectful and rude? Was it someone passive aggressive who was dragging their feet? Or was it just someone with a different perspective who worked differently than you? (Some people are irritated easily and are constantly annoyed with everyone but no one wants to hire someone who is high maintenance.)


  • Don’t say: “I’ve never had to work with someone difficult!” (That’s a lie)
  • Don’t put the other person down or make any kind of personal attacks: “They’re stupid – no one likes them!” (Even if it’s true)


  • Demonstrate in your answer to the interviewer that just because you wouldn’t spend time with someone outside of the office, that doesn’t mean you can’t work with them, and that you have worked with difficult people in the past

You might say:

“I don’t let my personal feelings about someone get in the way of getting the job done. I’m here to achieve a result, not to focus on someone’s character flaws. If that person is actively preventing me from getting my job done, then I will pull that person aside to understand what is going on and what the problem is, and if that doesn’t work I will escalate the problem to a senior manager for resolution. But thankfully that’s never happened. The bottom line is that I’ve been hired to deliver a result and I will do so in a professional manner regardless of how I feel about someone personally”. 

4. Tell me about a time you had a disagreement with your boss and how you handled it?

Job Interview

Everyone has disagreed with their boss about something. Even if you love your boss you’re never going to see eye to eye with them on everything.

Why interviewers ask questions about disagreement with management

  • How do you react when you disagree with your boss? Do you speak up or do you just keep it to yourself and go with the flow?
  • Are you difficult or easy to manage?
  • Are you a kiss ass?
  • Will you drag your feet?
  • Can you respect authority?
  • Can you manage up when necessary?
  • How often do these ‘disagreements’ come up?


  • Don’t talk badly about your boss or their management style no matter how bad they are. Even if you are only telling the truth, it will make you sound negative and it will raise red flags to the interviewer that you will speak negatively about your next boss (potentially them)
  • Don’t try to pretend that you’ve never had a disagreement with your boss
  • Don’t share a story in which your boss was right and you were wrong
  • Don’t go into all of the reasons as to why your boss was wrong


  • Stick to the facts
  • Speak calmly and objectively without emotion
  • You want to emphasize that you respect your bosses authority and ultimately whatever the boss says goes. You may disagree on some things, but that doesn’t mean that you won’t do what your boss wants you to do.

For example:

“I once had a disagreement with my boss over the best way to help a customer. Instead of disagreeing with him publicly in front of the other staff, I decided to wait until the meeting was over and then I asked to meet with him behind closed doors to discuss my rationale. Once I was able to clearly demonstrate to my manager that I understood where he was coming from, what he was saying and what he wanted to achieve, but just had other ideas as to the best way to go about it, he dropped his guard and was willing to hear me out and to consider other ideas.”

3. What is the most stressful situation you’ve ever been in at work?  

Job Interview

Everyone has experienced stressful situations at work, but obviously not everyone deals well with stress.

Some people handle stress better than others and some people even work better under pressure. Without a deadline of some kind they tend to coast.

Why interviewers ask questions about stress:

  • If you’re interviewing for a job within a highly pressurized environment the interviewer needs to know you can cope (not everyone can)
  • Some people work well under pressure, others don’t. How about you? How do you handle pressure? Can you rise to the occasion when the situation demands it? Or do you freak out and start panicking? That’s what the interviewer wants to know.
  • Sometimes – but not always – the best predictor of future behavior is past behavior. If the interviewer knows you have dealt with stressful situations in the past, especially a major crisis, you are more likely to be able to deal with them in the future


  • Don’t say you don’t feel pressure/stress as the interviewer probably won’t believe you. (It’s like saying you have no weaknesses.)
  • Don’t say you can’t handle stress. (It might be true, but saying so will probably cost you the job)


  • Ideally, you want to share a story of having worked in a highly stressful situation with super tight deadlines, angry customers, fighting co-workers etc. where the interviewer thinks: “If they can handle that – they can handle anything!”

From my own experience I could say: “When I recruited for the ANZ Bank we had a super strict KPI deadlines of 48 hours to provide 2 highly suitable and qualified candidates to the hiring managers. Failure to consistently deliver meant that we could be kicked off the preferred supplier panel which would have cost our company tens of millions of dollars.”

You should also talk about other ways you deal with stress and pressure such as:

  • Having a written list of goals and prioritizing which tasks are most important
  • Focusing on the task at hand and not on the drama/pressure surrounding it
  • De-stressing before/after work by exercising/meditation/running/swimming/yoga

2. What is your greatest weakness?

Job Interview

Why do interviewers still ask this annoying cliché question?

You came here to sell yourself and now they’re asking you this crap?

Why interviewers ask questions about weakness:

  • To see how honest and self-aware you are
  • To know what areas you need to work on improving
  • To put you on the spot to see how you deal with pressure
  • To get a REAL feel for who you are and to see if you’ll admit to something you wouldn’t ordinarily had they not asked


Don’t lie and try to pretend you have NO weaknesses or attempt to BS the interviewer by giving strengths disguised as weaknesses:

“I work too hard”

“I care too much”

“I’m a perfectionist”

This won’t work. If you try to answer questions about weakness by giving a strength disguised as a weakness most interviewers will know you’re lying and it’ll probably cost you the job. Most interviewers will think: “I can’t trust this person. They’re not honest. They’re trying to hide something…”

They might even ask you a series of follow up questions:

“How has this weakness affected you negatively?”

“What other weaknesses do you have?”

“What would your manager say is your greatest weakness?”

So don’t lie and try to pretend you have no weaknesses.

You also don’t want to give a personality trait as a weakness that can’t be easy corrected or ‘fixed’:

“I’m lazy”

“I’m shy”

“I’m selfish”

Nor do you wish to give a weakness that is unattractive to all employers:

“I’m a slow learner” 

“I’m hard to get along with”

I’m not a team player” 


  • Share a real weakness (not a strength disguised as a weakness), that ISN’T critical to the main responsibilities of the job you’re applying for and won’t immediately disqualify you

Ideally, you also want to share a weakness that can easily be fixed or improved upon and talk about what you’re doing to correct it. This way you demonstrate self-awareness and proactivity and get the interviewer once again focused on your strengths instead of your weaknesses.

Personally, my 3 greatest weaknesses on the job are:

  • Public speaking
  • Impatience
  • I get bored easily

I could answer this way. “My greatest weakness is nervousness when public speaking. (Which is not one of the main requirements of my job in recruitment). I found in the past that whenever I had to give a speech inside/outside of work I would get nervous. So I decided to do something about it by joining Toastmasters which has significantly improved my public speaking ability and presentation skills.”

Again, don’t share a weakness that is critical to the main responsibilities of the job you are applying for because that would immediately disqualify you.

For example: If you’re applying for a job in sales, you don’t want to tell the interviewer “customer service” is your greatest weakness. But you might mention lack of experience with a certain software application commonly used in sales that you could easily learn and come up to speed with.

Potential answers to the weakness question include:

“I can be direct and to the point especially when we’re fast approaching an important deadline which can come across as rude.” (If you’re applying for a fast paced and busy role in which direct communication is likely to be an asset)

“I lack experience in XYZ software but I’m doing my best to come up to speed with it in my spare time after hours by watching tutorials on guru99 and YouTube.”

“I don’t have a lot of experience within the banking sector.” (A ‘nice to have’ if you’re applying for a job within the banking sector that also shouldn’t be a deal breaker)

“Working in sales I can sometimes take rejection personally. I need to realise that it’s about the product or the pitch, not about me.”

Don’t be afraid to share a weakness. Nobody’s perfect. Everyone has lots of weaknesses. Just think carefully about what weakness you wish to share.

1. Tell me about the biggest mistake you’ve ever made in the workplace?

Job Interview

Everyone makes mistakes. I do. You do. We all do.

However, whilst everyone makes mistakes, not everyone learns from their mistakes or is adult enough to take responsibility for them. Most people just try to point fingers and blame others for their mistakes.

Why interviewers ask questions about past mistakes:

  • To find out how honest/self-aware you are
  • To find out if you can admit to your mistakes
  • To find out if you can take responsibility for your mistakes
  • To find out what you have learnt from your mistakes


  • Don’t try to pretend you’ve never made a mistake (that’s a lie)
  • Don’t blame others for your mistakes
  • Don’t share a catastrophic mistake that is likely to alarm the interviewer


  • Share a situation in which you made a mistake, ideally a minor one, and what you learnt from it. You want to talk about what you have learnt from your mistake, and why it is unlikely to happen again

Final thoughts

Job Interview

It doesn’t matter if you’re interviewing for a role in banking/finance, IT, sales or anywhere else. You NEED to know how you’re going to answer these questions.

Most of these questions are only difficult if you’re unprepared, and the more unprepared you are, the more difficult they will be.

Be smart: Don’t just turn up to your next interview hoping you don’t get asked these questions. Instead, prepare for the worst and expect that every single one of these questions will be asked of you and KNOW how you’re going to answer them ahead of time and what examples you will use to illustrate your point. What did you do? How did you do it? Have an example ready for the interviewer which is easy to follow and highlights your relevant skills and abilities.

In an interview ANY small leak can sink the ship. You don’t want to let one unanswered/poorly answered question be the reason you don’t get the job. Remember: Employers are looking for reasons to eliminate candidates from the process when there is too much competition.

When you get asked these questions, don’t answer hypothetically or by giving fake examples or my examples. Don’t try to avoid or ignore the question by talking round and round in circles. Instead, answer the question directly and succinctly to the point citing specific examples relevant to the question of the interviewer.

Your answers need to be your own, and they need to be honest, well rehearsed and congruent.

Remember: S.T.A.R – Situation, Task, Action, Result.

Situation – What was the situation?

Task – What was your task?

Action – What did you do?

Result – What was the result?

The key to successful interviewing and answering each of these questions is:

  • Preparation: The more preparation you do, the less of an issue it will be when you are asked these questions and the less you will feel under pressure and ‘put on the spot’.
  • Selective honesty: You don’t want to lie about anything, but you do want to select truthful examples that will help you to pass the tests of the interviewer and not raise any red flags.

Why do interviewers ask these difficult questions? Because they want to get the truth out of you. They want to know who you really are. Anyone can talk about their strengths, but what are your weaknesses? What are you like when you’re put under pressure? What are you like outside of your comfort zone? That’s what the interviewer really wants to know.

All of these difficult questions are asked for a reason.

The interviewer wants to know:

  • How you think
  • How you make decisions
  • How you solve problems
  • How you handle conflict
  • How you handle stress
  • How you manage your time
  • Are you a good communicator
  • Are you emotionally intelligent
  • Can you work with different kinds of people and personalities
  • Do you have a history of conflict with colleagues or management
  • Do you play office politics
  • Are you adaptable
  • Are you resourceful
  • Will you be challenged
  • Will you be overwhelmed
  • Will you stay in the job
  • Are you management material

If you’re in the job hunt, I also highly recommend you check out my other articles:

35 Interview mistakes to avoid: Interview Mistakes

How to get your dream job: Dream Job

25 CV mistakes to avoid: CV Mistakes

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